1. Field of the Invention
This invention relates to novel .DELTA..sup.4 -3-oxo-etianic acids which are substituted at the 4-position with fluoro, chloro or bromo and are optionally substituted at the 6-position with fluoro or chloro and at the 9-position with fluoro, chloro or bromo. The compounds are active anti-inflammatory agents in mammals. The invention further relates to pharmaceutically active compositions comprising a compound of the invention in combination with pharmaceutically acceptable excipient. The invention also relates to a process for preparing the compounds of the invention.
2. Prior Art
It is known that .DELTA..sup.4 -3-keto-etianic acids which are substituted at the 9 position with chlorine or fluorine and at the 11 position with keto or hydroxy or chloro group. See for example U.S. Pat. No. 3,828,080 to Phillipps. In addition certain 4-fluoro and 4-chloro substituted steroids of the pregnane series are known. See, for example, U.S. Pat. No. 3,232,960 to Magerlein and U.S. Pat. No. 3,707,537 to Kierstead. It is also known that certain 3-keto-etianic acids and esters may be substituted at both the 9.alpha. and 6.alpha. positions with fluoros. See for example, U.S. Pat. No. 4,093,721 to Phillipps and U.S. Pat. No. 3,036,010 to Anner.
A heretofore unknown series of .DELTA..sup.4 -3-keto-etianic acids being substituted at the 4 position with fluoro, chloro or bromo has been discovered and is disclosed herein. The compounds exhibit superior anti-inflammatory activity as compared to other etienic acid derivatives which are already known.